4.4 Article

A Facile One-Pot Solvent-Free Synthesis, in Vitro and in Silico Studies of a Series of Tetrahydropyridine Derivatives as Breast Cancer Inhibitors

Journal

CHEMISTRYSELECT
Volume 8, Issue 43, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202302533

Keywords

Ammonium trifluoroacetate; Cancer; Molecular docking; Multicomponent reactions; Tetrahydropyridines

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Ammonium trifluoroacetate (ATA) catalysed synthesis of 1,2,5,6-tetrahydropyridine (THP) derivatives under eco-friendly conditions using a facile one-pot strategy is reported. Molecular docking simulation and in vitro inhibitory activity evaluation on MCF-7 breast cancer cell lines identified four potential hit candidates among the synthesized compounds. These compounds hold promise as potential lead molecules.
Ammonium trifluoroacetate (ATA) catalysed synthesis of 1,2,5,6-tetrahydropyridine (THP) derivatives, under eco-friendly conditions via a facile one-pot strategy. We have synthesized fifteen THP derivatives, and docked into the crystal structure of Phosphatase and Tensin Homolog deleted on Chromosome 10 (PTEN) tumour suppressor protein (PDB ID: 1D5R) based on drug-likeness prediction and pharmacokinetic properties. Molecular docking simulation studies reveal that four of our synthesised compounds are potential hit candidates because they bound to the receptor through 5-7 conventional hydrogen bonds with -9.7 to -8.6 kcal/mol of binding energy. The compounds were evaluated using the in vitro inhibitory activity of MCF-7 breast cancer cell lines. Identified hit compounds showed moderate inhibition at (160-320 mu g/mL) and inhibitory concentration IC50 values in the low micromolar range of 171.062, 189.803, 195.469 and 181.272 mu g/mL respectively. The results obtained are very promising; therefore fine-tuning the substituents of hit molecules with appropriate bioisosteres can lead to the development of potential leads. Ammonium trifluoroacetate (ATA) catalysed synthesis of 1,2,5,6-tetrahydropyridine (THP) derivatives, under eco-friendly conditions via a facile one-pot strategy has been repoted. Molecular docking simulation studies followed by in vitro inhibitory activity of MCF-7 breast cancer cell lines for the synthesized THP derivatives were performed and the studies reveal that four of the fifteen synthesised compounds are found as potential hit candidates.image

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